Acetone → HCID 86596084, compound

HRID 1823797Notes

Reaction equation

HRID 1823797 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[O:12])[NH:7][C:6]=2[CH:21]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C.C[C:42]([CH3:44])=[O:43]>>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][C:11](=[O:12])[NH:10][C:8]1[NH:7][C:6]2[CH:21]=[C:2]([O:1][S:30]([C:24]3[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:23]=3[F:22])(=[O:32])=[O:31])[CH:3]=[CH:4][C:5]=2[N:9]=1.[C:42]([OH:31])(=[O:43])[C:44]1[CH:4]=[CH:3][CH:2]=[CH:21][CH:6]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 22146802HCID 22146802, compound

Product 1

HCID 86596084HCID 86596084, compound

Procedure

A stirred solution of 1-(6-hydroxy-1H-benzoimidazol-2-yl)-3-pyridin-2-ylmethyl-urea (50 mg, example 83-a) and 2,6-difluoro-benzene-sulfonyl chloride (38 mg) in acetone (1 ml) was treated with triethylamine (48 μl). After stirring at ambient temperature for 4 hours, the reaction mixture was evaporated. The residue was filtered and the filtrate evaporated. The residue was directly purified by LC/MS triggered purification to give benzoic acid 2,6-difluoro-benzenesulfonic acid 2-(3-pyridin-2-ylmethyl-ureido)-3H-benzoimidazol-5-yl ester (29.6 mg) as a off-white solid Mass spectrum: 427 [M+H]+; retention time=7.86 minutes.

Workup

  1. customthe reaction mixture was evaporated
  2. filtrationThe residue was filtered
  3. customthe filtrate evaporated
  4. customThe residue was directly purified by LC/MS
  5. custompurification

Sources & evidence

ORD record
ord-33f615bb96b644f2948eecfdfc36564e
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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